Therapeutical compounds containing metal abietates



Patented Feb. 16, 1937 THERAPEUTICAL COMPOUNDS CONTAIN- 'ING METAL ABIETATES Alien 1.. Omphundro and Emil c; Fanto; Fairiield, Conn, assignors to McKesson 8: Robbins, Inc., a corporation of Maryland No Drawing.

Application November 1'1, 1984, Serial No. 753,545

10 Claims. (CL 167-88) This invention relates to a method of producing bland petroleum-hydrocarbon solutions of chemically pure metal abietates, based on the present accepted structural formula oi abietic.

CaH1

soluble in common solvents like benzene, ether,

' acetone, carbon tetrachloride, chloroiorm, etc.

These solvents are not adaptable for therapeutical 30 or medical use as they are too irritating on exposed body surfaces or mucous membranes.

In accordance with our present invention, we propose these compounds, which we have found to possess eil'ective bacteriological properties, for

5 therapeutical or medicinal uses.

Because of the necessity of using bland oils or bland mixtures for that purpose, we attempted to employ liquid petrolatum U. B. P. X (petroleum hydrocarbons or U. S. P. X standard purity) but 40 iound they could not be used for that purpose be-- cause the metal abietates are not soluble in those oils. 1

We discovered that. by dissolving or dispersing the metal abietate in some 01' the following essen- 45 tial oils or their main constflzuents; intermiscible with petroleum hydrocarbon oils, the antiseptic efllciency was not altered.

A selected list of the most economical or most prominent types of those oils areas follows, and

were found to serve that purpose.

Citrus oils (lemon, orange, etc.)

Turpentine Oil pine Oil conaiba Oil eucalyptus I 5 Eucalyptol -&

Oiinadeput containing as main constituentsz.

Terpines flesquiterpes I Terpin esters Terpin anhydride They dissolve metal abietates and are also miscible with esters of abietic acid and petroleum hydrocarbons. I

We found further that to facilitate this dissolving process, the use of purified alkyl esters 01 natural wood resin or alkyl esters of abietic acid in addition to the petroleum oils, is of 'good advantage to produce clear solutions, without impairing the antiseptic properties of the compounded mixture, The'se alkyl esters are good solvents for all petroleum hydrocarbons. We found that they were intermiscible with the solutions of metalabietates in organic chemicals or essential oils as explainedbeiore.

We found that'20% to 45% of the metal abletates, particularly silver abietate, may be kept in the essential oils or related chemical substances in solution.

For practical purposes, we found that not more than 31% metal abietate is necessary in the compounded mixture to give theantiseptic efficiency required for therapeutical use. To dissolve that amount of metal abietate in the essential oils or related chemical substances will require not less than 30% ct abietic acid esters to 70% petroleum hydrocarbons.

(1) The emciency in regard to antiseptic action 40 can be easily demonstrated by using the petri dish agar medium penetration test, the so-called I-Iimebaugh technique, as described in Bulletin No. 198, December, 1931, of the U. S. Department of Agriculture, using as the organism of ex- 5 perimentation, staphylococcus aureus, the wellknown standard organism for testing bactericidal eiiiciency.

(2) Or the yeast fermentation inhibition, using a technique similar to the Pilcher, Sollman and Leech method by measuring their inhibiting effect on yeast-sugar fermentation.

To illustrate on a sample, our method of preparing and compounding, we proceedsubstantially as follows, l-abietic acid was made according to the directions or Steele (J. Am. Chem. Soc, 44, 1333, 1922) from American wood resin. This product is recrystallized several times from methanol and dried in This purified acid is converted into the potassium salt'of the l-abietic acid andthen converted into the silver salt. 0.2 gr. silver abietate. after purification, is triturated with 0.8 cc. eucalyptol U. S. P. until a clear solution is obtained. Then 30 cc. abietic acid methyl ester is added; preferably for better color and stability, vacuum distilled. abietic acid methyl ester or abieticacid methyl ester hydrogenated is used, and now, under constant stirring.

69 cc. liquid petrolatum is mixed in. After allowing to stand a few days and filtering, a clear stable, nearly water-white solution is obtained.

The scope of this invention is to be determined by-reierence to the following claims, said claims to be interpreted as broadlyas possible,- consistent with the state of the art.

We claim as our invention:

1. A.bland therapeutic composition containing an abietate-of a metal selected from the group consisting of silver, bismuth, mercury and zinclower alkyl ester of abietic acid, and liquid petrolatum.

4. A therapeutic compoaitioncontaining 'a mercury abietate dissolved in eucalyptus oil and dispersed in a lower alkyl ester of abietic acid, and a petroleum hydrocarbon.

5. A therapeutic composition containing 9. bismuth abietate dissolved in eucalyptus oil and dispersed in a lower alkyl ester of abietic acid, and liquid petrolatum.

6. A therapeutic composition containing an abietate of a. metal selected from the group con: sisting of silver, bismuth, mercury and zinc dissolved in eucalyptol and dispersed in a lower alkyl ester of abietic acid, and a petroleum hydrocarbon oil.

I. A bland therapeutic composition containing an abietate or a metal selected from the group consisting of silver, bismuth, mercury and zinc dissolved in an essential oil which is a solvent of said abietate and dispersed in a hydrogenated alkyi ester of abietic acid, and liquid petrolatum.

8. A bland therapeutic composition containing an aibetate of a metal selected from the group consisting oi silver, bismuth, mercury, and zincdissolved in an essential oil which is a solvent of said abietate and dispersed in a hydrogenated methyl ester of abietic acid, and liquid petrolatum.

9. The method of preparing a bland therapeu-' tic composition which consists in dissolving an abietate of a metal selected from the group consisting of silver, mercury, bismuth, and zinc, in an essential oil which is a solvent for said metal abietate, adding a lower albl ester 01' abietic acid, and, under constant stirring, incorporating a petroleum hydrocarbon oil.

10. The method of preparing a bland therapeutic composition which consists in dissolving'an abietate of a metal selected from the group consisting of silver, mercury, bismuth, and zinc, in an essential oil which is a solvent for said metal abietate, adding a lower allwl ester of abietic acid and, under constant stirring, incorporating a liquid petrolatum.

ALLEN L. OMOHUNDRO. EMU; C. FANTO. 

